Chesterfield Travel Guide

Tourist Guide

15%+ off winter escapes close to home

Book a getaway and you can save on select hotels and homes.¹
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundable
The price is NZ$206 per night from 24 May to 25 May
NZ$206
24 May - 25 May
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (938 reviews)
Nice for families, has kitchen facilities for cooking. Door to room needs attention. Had to slam hard to close. Nice big bathroom. Thought we were getting 2 beds but had king bed and pull out couch. Wouldn’t always work for everyone. Could hear dog barking in nearby room. Price was right

Reviewed on 17 May 2026

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
The price is NZ$181 per night from 31 May to 1 June
NZ$181
31 May - 1 June
includes taxes & fees
Stay at this golf hotel in West Springfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
7/10 Good! (1,017 reviews)
Good!

Reviewed on 17 May 2026

Quality Inn West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
The price is NZ$339 per night from 21 May to 22 May
NZ$339
21 May - 22 May
includes taxes & fees
Stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants and room service. Our guests praise the breakfast and the pool in their reviews. Popular ...
9.2/10 Wonderful! (2,237 reviews)
Excellent staff and very convenient location to UMass Amherst and right next door to Northampton. We had a one bedroom suite which was very spacious and comfortable. We had dinner next door at Delaney's for my son's graduation and everything was amazing. The weekend couldn't have worked out any better! ...

Reviewed on 18 May 2026

D. Hotel Suites & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (236 reviews)
Great spot on the water!

Reviewed on 23 Apr 2026

Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket MA
Stay at this cabin in Becket. Enjoy a garden, laundry facilities and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake

Otis MA
Stay at this cottage in Otis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Old Baldy Wildlife Sanctuary and Otis Ridge are located ...
9.6/10 Exceptional! (39 reviews)
We enjoyed this cozy cabin very much, the host was attentive, she checked in with us upon our arrival, and answered our questions immediately. Everything was exactly as described. It was the perfect stay for a weekend getaway!

Reviewed on 8 Dec 2025

Cozy Cottage-Sunset On The Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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